JPH02262562A - イミダゾール系化合物 - Google Patents

イミダゾール系化合物

Info

Publication number: JPH02262562A
Authority: JP; Japan
Prior art keywords: group; compound; reaction; chloro; phenylimidazole
Prior art date: 1988-10-20
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

JP1268716A

Other languages

English (en)

Japanese (ja)

Inventor

Itaru Shigehara

重原　格

Toshio Nakajima

俊雄中島

Shigeyuki Nishimura

重幸西村

Takeshi Oshima

武大嶋

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Ishihara Sangyo Kaisha Ltd

Original Assignee

Ishihara Sangyo Kaisha Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1988-10-20

Filing date

1989-10-16

Publication date

1990-10-25

1989-10-16 Application filed by Ishihara Sangyo Kaisha Ltd filed Critical Ishihara Sangyo Kaisha Ltd

1989-10-16 Priority to JP1268716A priority Critical patent/JPH02262562A/ja

1990-10-25 Publication of JPH02262562A publication Critical patent/JPH02262562A/ja

Status Pending legal-status Critical Current

Links

RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title claims description 45
-1 Imidazole compound Chemical class 0.000 title claims description 22
125000000217 alkyl group Chemical group 0.000 claims abstract description 26
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 21
125000003545 alkoxy group Chemical group 0.000 claims abstract description 19
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
229910052801 chlorine Inorganic materials 0.000 claims description 9
125000001309 chloro group Chemical group Cl* 0.000 claims description 9
125000005843 halogen group Chemical group 0.000 claims description 7
239000000126 substance Substances 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
150000001875 compounds Chemical class 0.000 abstract description 93
239000003795 chemical substances by application Substances 0.000 abstract description 11
238000004519 manufacturing process Methods 0.000 abstract description 8
239000000417 fungicide Substances 0.000 abstract description 2
239000000463 material Substances 0.000 abstract description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
230000000855 fungicidal effect Effects 0.000 abstract 1
230000001473 noxious effect Effects 0.000 abstract 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
238000006243 chemical reaction Methods 0.000 description 71
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 37
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
239000002904 solvent Substances 0.000 description 29
239000000203 mixture Substances 0.000 description 26
238000002844 melting Methods 0.000 description 25
230000008018 melting Effects 0.000 description 25
238000003786 synthesis reaction Methods 0.000 description 20
230000015572 biosynthetic process Effects 0.000 description 19
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
150000002460 imidazoles Chemical class 0.000 description 16
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
239000007795 chemical reaction product Substances 0.000 description 14
239000000047 product Substances 0.000 description 13
150000003839 salts Chemical class 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 12
238000010898 silica gel chromatography Methods 0.000 description 12
238000003756 stirring Methods 0.000 description 11
239000002253 acid Substances 0.000 description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
238000010992 reflux Methods 0.000 description 9
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
229910052500 inorganic mineral Inorganic materials 0.000 description 8
238000000034 method Methods 0.000 description 8
239000011707 mineral Substances 0.000 description 8
235000010755 mineral Nutrition 0.000 description 8
239000007787 solid Substances 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
239000012299 nitrogen atmosphere Substances 0.000 description 7
239000002994 raw material Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 6
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 6
239000012467 final product Substances 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
230000003902 lesion Effects 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
241000607479 Yersinia pestis Species 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
230000009435 amidation Effects 0.000 description 4
238000007112 amidation reaction Methods 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
235000011114 ammonium hydroxide Nutrition 0.000 description 4
229940125782 compound 2 Drugs 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000001914 filtration Methods 0.000 description 4
230000003472 neutralizing effect Effects 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
229940126062 Compound A Drugs 0.000 description 3
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000000370 acceptor Substances 0.000 description 3
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
229940040526 anhydrous sodium acetate Drugs 0.000 description 3
229940125904 compound 1 Drugs 0.000 description 3
229940125898 compound 5 Drugs 0.000 description 3
239000013078 crystal Substances 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
JFCHSQDLLFJHOA-UHFFFAOYSA-N n,n-dimethylsulfamoyl chloride Chemical compound CN(C)S(Cl)(=O)=O JFCHSQDLLFJHOA-UHFFFAOYSA-N 0.000 description 3
125000004430 oxygen atom Chemical group O* 0.000 description 3
CVXGFPPAIUELDV-UHFFFAOYSA-N phenacylazanium;chloride Chemical compound [Cl-].[NH3+]CC(=O)C1=CC=CC=C1 CVXGFPPAIUELDV-UHFFFAOYSA-N 0.000 description 3
239000001632 sodium acetate Substances 0.000 description 3
235000017281 sodium acetate Nutrition 0.000 description 3
238000012360 testing method Methods 0.000 description 3
KOHMWXQESRAQEG-UHFFFAOYSA-N 1-amino-5-chloropentan-2-one;hydrochloride Chemical compound Cl.NCC(=O)CCCCl KOHMWXQESRAQEG-UHFFFAOYSA-N 0.000 description 2
DNYQVSBOGCMIDZ-UHFFFAOYSA-N 4-chloro-2-cyano-n,n-dimethyl-5-phenylimidazole-1-sulfonamide Chemical compound CN(C)S(=O)(=O)N1C(C#N)=NC(Cl)=C1C1=CC=CC=C1 DNYQVSBOGCMIDZ-UHFFFAOYSA-N 0.000 description 2
PZSLFKCLKJWPCU-UHFFFAOYSA-N 4-chloro-5-(3-chloropropyl)-1-(methoxymethyl)imidazole Chemical compound COCN1C=NC(Cl)=C1CCCCl PZSLFKCLKJWPCU-UHFFFAOYSA-N 0.000 description 2
XHLKOHSAWQPOFO-UHFFFAOYSA-N 5-phenyl-1h-imidazole Chemical compound N1C=NC=C1C1=CC=CC=C1 XHLKOHSAWQPOFO-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 2
239000012320 chlorinating reagent Substances 0.000 description 2
238000005660 chlorination reaction Methods 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
239000000539 dimer Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
125000004434 sulfur atom Chemical group 0.000 description 2
GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
MEFKFJOEVLUFAY-UHFFFAOYSA-N (2,2,2-trichloroacetyl) 2,2,2-trichloroacetate Chemical compound ClC(Cl)(Cl)C(=O)OC(=O)C(Cl)(Cl)Cl MEFKFJOEVLUFAY-UHFFFAOYSA-N 0.000 description 1
GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
WIHMGGWNMISDNJ-UHFFFAOYSA-N 1,1-dichloropropane Chemical compound CCC(Cl)Cl WIHMGGWNMISDNJ-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
VQIPXTITGUAIBB-UHFFFAOYSA-N 1-bromo-5-chloropentan-2-one Chemical compound ClCCCC(=O)CBr VQIPXTITGUAIBB-UHFFFAOYSA-N 0.000 description 1
SFOYQZYQTQDRIY-UHFFFAOYSA-N 1-chloro-3-iodopropane Chemical compound ClCCCI SFOYQZYQTQDRIY-UHFFFAOYSA-N 0.000 description 1
SEULWJSKCVACTH-UHFFFAOYSA-N 1-phenylimidazole Chemical compound C1=NC=CN1C1=CC=CC=C1 SEULWJSKCVACTH-UHFFFAOYSA-N 0.000 description 1
PEJQKHLWXHKKGS-UHFFFAOYSA-N 2,2,4,4,6,6,8,8-octachloro-1,3,5,7-tetraza-2$l^{5},4$l^{5},6$l^{5},8$l^{5}-tetraphosphacycloocta-1,3,5,7-tetraene Chemical compound ClP1(Cl)=NP(Cl)(Cl)=NP(Cl)(Cl)=NP(Cl)(Cl)=N1 PEJQKHLWXHKKGS-UHFFFAOYSA-N 0.000 description 1
WBQTVZALNOJHNB-UHFFFAOYSA-N 2-(methoxymethyl)-1h-imidazole Chemical compound COCC1=NC=CN1 WBQTVZALNOJHNB-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
HVSLODLVJGBOIZ-UHFFFAOYSA-N 4-chloro-n,n-dimethyl-5-phenylimidazole-1-sulfonamide Chemical compound CN(C)S(=O)(=O)N1C=NC(Cl)=C1C1=CC=CC=C1 HVSLODLVJGBOIZ-UHFFFAOYSA-N 0.000 description 1
XVRIEWDDMODMGA-UHFFFAOYSA-N 5-chloropentan-2-one Chemical compound CC(=O)CCCCl XVRIEWDDMODMGA-UHFFFAOYSA-N 0.000 description 1
235000001674 Agaricus brunnescens Nutrition 0.000 description 1
UHNRLQRZRNKOKU-UHFFFAOYSA-N CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O Chemical compound CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O UHNRLQRZRNKOKU-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 1
235000009849 Cucumis sativus Nutrition 0.000 description 1
240000008067 Cucumis sativus Species 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241000233679 Peronosporaceae Species 0.000 description 1
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
DRUIESSIVFYOMK-UHFFFAOYSA-N Trichloroacetonitrile Chemical compound ClC(Cl)(Cl)C#N DRUIESSIVFYOMK-UHFFFAOYSA-N 0.000 description 1
QUHHWZBUNMJHCE-UHFFFAOYSA-N [B+3].CC[O+](CC)CC Chemical compound [B+3].CC[O+](CC)CC QUHHWZBUNMJHCE-UHFFFAOYSA-N 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229940061627 chloromethyl methyl ether Drugs 0.000 description 1
229940125797 compound 12 Drugs 0.000 description 1
229940125758 compound 15 Drugs 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
KJDVGGASZPVNDW-UHFFFAOYSA-N ethyl 4-chloro-5-(3-chloropropyl)-1-(dimethylsulfamoyl)imidazole-2-carboxylate Chemical compound CCOC(=O)C1=NC(Cl)=C(CCCCl)N1S(=O)(=O)N(C)C KJDVGGASZPVNDW-UHFFFAOYSA-N 0.000 description 1
DNBIUWPIJOWUEU-UHFFFAOYSA-N ethyl 5-phenyl-1h-imidazole-2-carboxylate Chemical compound N1C(C(=O)OCC)=NC(C=2C=CC=CC=2)=C1 DNBIUWPIJOWUEU-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000007789 gas Substances 0.000 description 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
239000010931 gold Substances 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
239000004312 hexamethylene tetramine Substances 0.000 description 1
235000010299 hexamethylene tetramine Nutrition 0.000 description 1
238000003898 horticulture Methods 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
239000005457 ice water Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910017053 inorganic salt Inorganic materials 0.000 description 1
238000011835 investigation Methods 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
238000002156 mixing Methods 0.000 description 1
YRRWNBMOJMMXQY-UHFFFAOYSA-N n,n-dimethylimidazole-1-sulfonamide Chemical compound CN(C)S(=O)(=O)N1C=CN=C1 YRRWNBMOJMMXQY-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
239000005051 trimethylchlorosilane Substances 0.000 description 1
230000000007 visual effect Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

JP1268716A 1988-10-20 1989-10-16 イミダゾール系化合物 Pending JPH02262562A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP1268716A JPH02262562A (ja)	1988-10-20	1989-10-16	イミダゾール系化合物

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
JP26486888		1988-10-20
JP63-264868		1988-10-20
JP30867888		1988-12-06
JP63-308678		1988-12-06
JP1268716A JPH02262562A (ja)	1988-10-20	1989-10-16	イミダゾール系化合物

Publications (1)

Publication Number	Publication Date
JPH02262562A true JPH02262562A (ja)	1990-10-25

Family

ID=26546720

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP1268716A Pending JPH02262562A (ja)	1988-10-20	1989-10-16	イミダゾール系化合物

Country Status (5)

Country	Link
US (1)	US5023336A (fr)
EP (1)	EP0365030B1 (fr)
JP (1)	JPH02262562A (fr)
DE (1)	DE68912704T2 (fr)
ES (1)	ES2061879T3 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1995004724A1 (fr) *	1993-08-11	1995-02-16	Nippon Soda Co., Ltd.	Derive d'imidazole et son procede de production, et substance anti-nuisibles

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0441481A (ja) *	1990-06-05	1992-02-12	Nippon Synthetic Chem Ind Co Ltd:The	イミダゾール類のハロゲン化方法
IE73235B1 (en) *	1991-03-25	1997-05-21	Akzo Nv	4-aryl-thiazole or imidazole derivatives
DE4139950A1 (de) *	1991-12-04	1993-06-09	Bayer Ag, 5090 Leverkusen, De	2-cyanobenzimidazole, ein verfahren zu ihrer herstellung und ihre verwendung und neue vorprodukte
US5565577A (en) *	1992-09-23	1996-10-15	Smithkline Beecham Corporation	Process for preparing 1-alkyaryl-2-alkyl-5-formylimidazole
US5484939A (en) *	1993-03-12	1996-01-16	Lonza Ltd.	2-substituted 5-chlorimidazoles
ES2108894T3 (es) *	1993-03-12	1998-01-01	Lonza Ag	Procedimiento para la preparacion de 5-cloroimidazoles eventualmente sustituidos en posicion 2.
US5777105A (en) *	1995-08-24	1998-07-07	Merck & Co., Inc.	Process for the preparation of imidazolyl macrolide immunosuppressants
US6713500B2 (en)	1999-08-19	2004-03-30	Ishihara Sangyo Kaisha Ltd.	Agent for controlling animal diseases caused by parasites
EP1211245A4 (fr) *	1999-08-19	2002-10-30	Ishihara Sangyo Kaisha	Agents permettant de luter contre les maladies animales engendrees par des parasites
FR2842804B1 (fr)	2002-07-29	2004-09-03	Sanofi Synthelabo	Derives de n-[phenyl(piperidin-2-yl)methyl]benzamide, leur preparation et leur application en therapeutique
FR2861074B1 (fr)	2003-10-17	2006-04-07	Sanofi Synthelabo	Derives de n-[phenyl(piperidin-2-yl)methyl]benzamide, leur preparation et leur application en therapeutique
WO2012123298A1 (fr)	2011-03-11	2012-09-20	F. Hoffmann-La Roche Ag	Composés antiviraux
RU2014117587A (ru)	2011-10-10	2015-11-20	Ф. Хоффманн-Ля Рош Аг	Противовирусные соединения
KR20140104030A (ko)	2011-12-16	2014-08-27	에프. 호프만-라 로슈 아게	Hcv ns5a의 억제제
CN103936678B (zh) *	2014-04-23	2016-04-27	西安近代化学研究所	一种4-氯-2-氰基-n,n-二甲基-5-(4’-甲基苯基)-1h-咪唑-1-磺酰胺的合成方法
CN104292166B (zh) *	2014-10-14	2016-04-27	西安近代化学研究所	4-氯-2-氰基-n,n-二甲基-5-对甲苯基咪唑-1-磺酰胺合成方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1339133C (fr) *	1987-03-13	1997-07-29	Rikuo Nasu	Derives de l'imidazole et compositions a base de ces derives pour l'elimination d'organismes nuisibles
DE3708292A1 (de) *	1987-03-14	1988-09-29	Basf Ag	Gegen einwirkung von licht stabilisierte polymere sowie neue imidazol-2-carbonsaeureanilide
DE3804545A1 (de) *	1988-02-13	1989-08-24	Basf Ag	Verfahren zur herstellung von imidazol-2-carbonsaeuren

1989
- 1989-10-16 JP JP1268716A patent/JPH02262562A/ja active Pending
- 1989-10-20 DE DE68912704T patent/DE68912704T2/de not_active Expired - Lifetime
- 1989-10-20 US US07/424,630 patent/US5023336A/en not_active Expired - Lifetime
- 1989-10-20 ES ES89119518T patent/ES2061879T3/es not_active Expired - Lifetime
- 1989-10-20 EP EP89119518A patent/EP0365030B1/fr not_active Expired - Lifetime

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1995004724A1 (fr) *	1993-08-11	1995-02-16	Nippon Soda Co., Ltd.	Derive d'imidazole et son procede de production, et substance anti-nuisibles

Also Published As

Publication number	Publication date
EP0365030A1 (fr)	1990-04-25
DE68912704D1 (de)	1994-03-10
ES2061879T3 (es)	1994-12-16
DE68912704T2 (de)	1994-06-30
EP0365030B1 (fr)	1994-01-26
US5023336A (en)	1991-06-11

Publication	Publication Date	Title
JPH02262562A (ja)	1990-10-25	イミダゾール系化合物
EP0239391B1 (fr)	1994-03-02	1,2,6,-Triphényl-4(1H)-pyridinones et pyridinethiones dérivés, leur préparation et utilisations
CA2087260A1 (fr)	1992-02-07	Alkylsulfonylpyrazoles aryliques substituees comme herbicide
JPH0641118A (ja)	1994-02-15	ピコリン酸誘導体及び除草剤
JPH03151367A (ja)	1991-06-27	３‐置換フェニルピラゾール誘導体又はその塩類及びその用途
JP5980807B2 (ja)	2016-08-31	Ｎ−スルホニル−置換オキシインドール類を製造する方法
CN115989226B (zh)	2026-04-21	制备jak抑制剂的方法和中间体
SE448459B (sv)	1987-02-23	4a,9b-trans-hexahydro-gamma-karbolinforeningar som mellanprodukter for framstellning av hexahydro-gamma-karbolinforeningar
JP4173599B2 (ja)	2008-10-29	６−ヒドロキシ−２−オキソ−１，２，３，４−テトラヒドロキノリンの製造方法
CZ285271B6 (cs)	1999-06-16	Způsob výroby insekticidně, akaricidně a nematocidně účinných sloučenin 2-aryl-5-(trifluormet hyl)pyrrolu
KR870001922B1 (ko)	1987-10-22	이미다졸 유도체의 제조방법
KR100641908B1 (ko)	2006-11-02	피리딘 유도체, 그의 제조방법, 및 제초제 중간체로서의용도
Nenajdenko et al.	2019	Synthesis and structural study of dichlorodiazadienes derived from para-nitro benzaldehyde
JPH02108670A (ja)	1990-04-20	イミダゾール系化合物
JP4879907B2 (ja)	2012-02-22	フェニル２−ピリミジニルケトン類の製造方法及びその新規中間体
JP2006528978A (ja)	2006-12-28	β−ラクタマーゼ阻害剤中間体を合成するための方法
JPH02262560A (ja)	1990-10-25	イミダゾール系化合物
JP6705111B2 (ja)	2020-06-03	トリアジノン化合物
JPH01168675A (ja)	1989-07-04	１，３−ジアルキルピラゾール−５−カルボン酸エステル類の製造法
JP2609147B2 (ja)	1997-05-14	２，４―ジアミノ―６―置換―ピリミジン―３―オキサイドの製造方法
JP2896949B2 (ja)	1999-05-31	１−（４−アシルフェニル）アゾール類の製造方法
JP3376481B2 (ja)	2003-02-10	ヘキサヒドロピリダジンの製造法
US5426187A (en)	1995-06-20	Process for the preparation of 4-hydroxy-5-substituted ethynylpyrrolo [2,3-d]pyrimidine intermediates
US4175948A (en)	1979-11-27	Substituted isoindoles
CZ284072B6 (cs)	1998-08-12	Způsob výroby 2-aryl-5-trifluormethylpyrrolových sloučenin

JPH02262562A - イミダゾール系化合物 - Google Patents

Info

Links

Classifications

Landscapes

Priority Applications (1)

Applications Claiming Priority (5)

Publications (1)

Family

ID=26546720

Family Applications (1)

Country Status (5)

Cited By (1)

Families Citing this family (16)

Family Cites Families (3)

Cited By (1)

Also Published As

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